71815-31-1

Basic information

• Product Name: 1-(4-(p-Tolyloxy)phenyl)ethanone
• Synonyms: 1-[4-(4-Methylphenoxy)phenyl]-ethanone
• CAS NO: 71815-31-1
• Molecular Formula: C₁₅H₁₄O₂
• Molecular Weight: 226.27
• Mol File: 71815-31-1.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-(p-Tolyloxy)phenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-(p-Tolyloxy)phenyl)ethanone(71815-31-1)
• EPA Substance Registry System: 1-(4-(p-Tolyloxy)phenyl)ethanone(71815-31-1)

Safety Data

• Hazardous Substances Data: 71815-31-1(Hazardous Substances Data)

Usage

Description

1-(4-(p-Tolyloxy)phenyl)ethanone, an aromatic ketone with the molecular formula C15H14O2, is a chemical compound featuring a phenyl ring with a p-tolyloxy group at the para position and a carbonyl group attached to the ethyl group. 1-(4-(p-Tolyloxy)phenyl)ethanone is known for its unique chemical properties and functionality, making it a valuable building block in organic synthesis and pharmaceutical research.

Uses

Used in Pharmaceutical Research:
1-(4-(p-Tolyloxy)phenyl)ethanone is used as a building block for the development of new drugs and fine chemicals, leveraging its unique chemical properties and functionality to create novel pharmaceutical compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 1-(4-(p-Tolyloxy)phenyl)ethanone serves as an essential component for creating a variety of complex organic molecules, contributing to the advancement of chemical research and innovation.
Safety Precautions:
It is crucial to handle 1-(4-(p-Tolyloxy)phenyl)ethanone with care, as it may pose risks to human health and the environment if not properly managed. Proper safety measures and disposal methods should be followed to minimize potential hazards.

Upstream product

• 1192-96-7 potassium p-cresolate 
• 99-90-1 para-bromoacetophenone 
• 1706-12-3 4-phenoxytoluene 
• 75-36-5 acetyl chloride 
• 106-44-5 p-cresol 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 62790-85-6 tert-Butyl(dimethyl)-(4-methylphenoxy)silane 
• 99-91-2 para-chloroacetophenone 
• 1121-70-6 sodium 4-methylphenoxide 
• 13329-40-3 4-Iodoacetophenone 
• 100-19-6 (4-nitrophenyl)ethanone 
• 403-41-8 1-(4-Fluorophenyl)ethanol 

Downstream Products

• 116218-31-6 3-Dimethylamino-2-dimethylaminomethyl-1-(4-p-tolyloxy-phenyl)-propan-1-one; hydrochloride 
• 86896-99-3 4-methylphenyl 4-(hydroxyisopropyl)phenyl ether 
• 86431-74-5 4-methylphenyl 4-(chloroisopropyl)phenyl ether 

Relevant articles and documents

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors

Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 μM, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20–200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin-resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes.

Design, synthesis and biological evaluation of uncharged catechol derivatives as selective inhibitors of PTP1B

Protein tyrosine phosphatases 1B (PTP1B) is a promising and validated therapeutic target to effectively treat T2DM and obesity. However, the development of charged PTP1B inhibitors was restricted due to their low cell permeability and poor bioavailability. Based on active natural products, two series of uncharged catechol derivatives were identified as PTP1B inhibitors by targeting a secondary aryl phosphate-binding site as well as the catalytic site. The most potent inhibitor 22 showed an IC50 of 0.487?μM against PTP1B and strong selectivity (27-fold) over TCPTP. Kinetic studies were also performed that 22 act as a competitive PTP1B inhibitor. The treatment of C2C12 myotubes with 22 markedly increased the phosphorylation levels of IRβ, Akt and IRS1 phosphorylation. The similarity of its action profiling with that produced by insulin suggested its potential as a new non-insulin-dependent drug candidate.